Cerous carbonate → 2-Chloro-6-(3,5-dimethoxyphenyl)-5-fluoroquinazoline

HRID 56479

반응식

HRID 56479 반응식
Br[C:2]1[C:3]([F:13])=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([Cl:12])[N:6]=[CH:5]2.[CH3:14][O:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1.C(=O)([O-])[O-].[Ce+3].C(=O)([O-])[O-].C(=O)([O-])[O-].[Ce+3]>C1COCC1.O.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[Cl:12][C:7]1[N:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:18]3[CH:17]=[C:16]([O:15][CH3:14])[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=3)[C:3]=2[F:13])[N:8]=1

참가 물질

7

반응물 3

HCID 160516Cerous carbonateHCID 4374257(3,5-Dimethoxyphenyl)boronic acidHCID 574611366-Bromo-2-chloro-5-fluoroquinazoline

생성물 1

HCID 1180361612-Chloro-6-(3,5-dimethoxyphenyl)-5-fluoroquinazoline수율 71.1%

시약·촉매·용매 3

HCID 178418851HCID 178418851, 화합물촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
80 °C

실험 절차

A mixture of 6-bromo-2-chloro-5-fluoroquinazoline (1.5 g, 5.74 mmol), 3,5-dimethoxyphenylboronic acid (1.15 g, 6.31 mmol), cerium carbonate (1.87 g, 5.74 mmol) and bis(tri-tert-butylphosphine)palladium (148 mg, 0.29 mmol) in THF (30 mL) and water (3 mL) was degassed with nitrogen for three times and stirred at 80° C. overnight. The mixture was cooled to room temperature and extracted with ethyl acetate (3×200 mL). The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (petroleum ether:ethyl acetate=8:1) to get the title product as a white solid (1.3 g, 70%). MS (ES+) C16H12ClFN2O2 requires: 318, found: 319, 321 [M+H]+.

후처리

  1. customwas degassed with nitrogen for three times
  2. temperatureThe mixture was cooled to room temperature
  3. extractionextracted with ethyl acetate (3×200 mL)
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography (petroleum ether:ethyl acetate=8:1)

출처 및 근거

ORD 기록
ord-9c3ceb70829d421fa82865e1e665d467
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434700B2

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